Building Total Rewards Statements That Actually Change Retention

Kelsey Willock Welcome Jessica O'Leary, Director of Benefits at Uplift Education. We are so excited to have you this Monday afternoon. To kick us off, I'd love for you to share a little bit about your career and background, where you're calling in from in your current role today. Jessica O'Leary Yes, so thank you for having me.

very excited to do this. ⁓ It's been a little while since I've done a podcast, so happy to kind of get back into the swing of things and answer all your questions. ⁓ Jessica O'Leary, Director of Benefits, again, at Uplift Education. We are a large charter school network in the DFW Metroplex.

So we have campuses that vary, excuse me, that spread from Dallas out into the Fort Worth area and down, of course, into South Dallas as well. I've been with Uplift for four and a half years as their Director of Benefits and before that I was with the City of Carrollton as their Benefits Administrator and before that started off my career in benefits and HR at Carrollton Farmers Branch ISD as their Benefits Specialist and Workers' Comp Specialist. So I've been in this game for oh gosh 13 years maybe going on 14.

So it's been a long journey, a lot has been learned and definitely, you know, always willing to share what I've learned, at least from my experience. Kelsey Willock Well, I'm really excited to ask you so many questions about your current role and where the market currently is at. I'm particularly interested as you come from education, which has its own unique challenges and different things about the benefit space. Before we get there, I want to get to know you personally a little bit more.

So please tell me, what is your earliest memory of money? Jessica O'Leary Mm-hmm. Oh gosh, my earliest memory of money. What I remember is, I think it was in like second grade.

And so me and my best friend who lived next door to me, we wanted to make our own money. So we're entrepreneurs early on. So we grabbed some of our old books that we weren't reading anymore, like for little kids, you know, because we were big girls now. So we actually decided to sell them outside on my front lawn.

And so as people were driving by, we'd like you'll have for sale, books for sale. We actually wrote out, you know, the amount of the book on the front of it on the cover page. And I only remember one person actually stopping. Otherwise, people kind of waved and giggled and thought it was cute.

And he was like concerned, dad, like, was watching you guys. But he did buy a book for his daughter. So that was my earliest memory of money, like trying to make my own money, seeing my parents work hard. I'm a daughter of a retired police officer and a teacher.

So Yeah, they're very strict on, you know, rules and being independent and things like that. So, you know, I always wanted to start off making my own. So always kind of was conscious of money and what it can do for you being a valuable resource for sure. Kelsey Willock and I'm sure they were very proud of you having your own pretty much Scholastic book fair on your front lawn.

What was your first job and do you recall what you did with your first paycheck? Jessica O'Leary yeah. Yes, so I worked with, I don't know if it's still in operation, but I'm from Milwaukee, Wisconsin. ⁓ There's an organization called Strive Media Institute.

So for any ⁓ students in high school who are interested in getting into communications, broadcast journalism, IT production, all of that. You can actually, you know, apply and work as an intern. And so they pretty much train you up in whatever field that you're interested in. So at the time I really liked computers, like I was a gamer.

So I actually helped with like fixing computers and got to actually work on fixing like motherboard and actually taking a computer apart. And it's like the big heavy desktop computer at the time. I think it was like a Hewlett Packard. And so that was fun just learning that.

And I honestly think my first paycheck, probably bought clothes. Cause I started that job right before school was starting. So I think that was my first time actually buying my own school clothes. And then after that, that was kind of the thing.

Like I would always have a job and that's what I would do with my money was getting school clothes. And then of course buying food at school or after school with friends. So it was kind of like those fun expenses that make you feel like you're an adult right out the gate of taking care of yourself with for things that normally you would wait on your parents to give you an allowance and pay for. Kelsey Willock And it just gives you a higher level of pride, right?

I paid for this. I didn't get this as a Christmas gift or something like that. I've got to ask though, what were the games that you were playing as a fellow big fan of those games? Jessica O'Leary Mm-hmm.

So I graduated high school in 2003. So at that time was like the first PlayStation. I did still have a Sega Genesis that worked sometimes. So I'm big into like the fighting games.

So was like Street Fighter. remember Streets of Rage, Tekken or Tekken. I hope I'm pronouncing it right. I remember playing like Spyro and then got more into like computer games.

So I love like Quest games and then I started playing Sims and that's when I started like stopping playing the actual games on the console and I was straight PC because the Sims got like such a huge hold on me and so now I play it again but I use the PS5. Kelsey Willock We won't stay on this topic for too long because I'm sure we could have the entire conversation be about open world gaming, but we know we've got lot of benefits and HR leaders listening, but I will digress, but we'll keep this conversation going offline, How do you think your money story has influenced how you think about paying benefits on behalf of your employees?

Jessica O'Leary Mm-hmm. Great. I think my money story, other than being an entrepreneur, it's kind of like as I learned what to do and what not to do with my money, I kind of focused more on the value of the dollar. So like when I pay for something, it's like, but what do I get for this?

Like, yeah, I can get a shirt, but what if there's a two for one deal or something? Okay, I want to buy that. Or, know, maximizing discounts and things like that, just being a little bit more conscious. I'm kind of looking into more of how I can get this dollar to stretch versus the I guess what's the word I'm looking for, immediate boost that you get from like, know, I bought this and I feel good because I bought this, you know, it's kind of like, okay, but what else could I done with that money?

So I hate having that level of regret if I feel like I ever wasted my money. Kelsey Willock You want to get the most out of it. Jessica O'Leary For sure. And so when it comes to benefits, I mean the same thing.

⁓ I have to look into, especially as a director, like exactly when it comes to the benefits plans that we are preparing for our employees and our whole health plan strategy, it's like, what are we giving our employees for what we're offering? And when it comes to the premiums that they're paying, what exactly do they get from that? So it's always looking into what's the most that we can get and provide to them. in exchange for their portion of premium because that impacts the amount of money they take home at the end of the day.

So we want to make sure we're providing as much as we can to give them a pretty comprehensive package that, again, is very valuable to them and making their life easier. Kelsey Willock So, you know, this is, think, a great segue into today's challenges. And so, you know, it's no secret, healthcare costs are higher than they used to be. And figuring out ways in which to deliver higher value while coupled with higher expenses can be a real challenge.

How do you think about continuing to deliver value for employees in this deeply complex time? Jessica O'Leary yeah. Mm-hmm. yeah.

mean, again, beyond just the cash compensation, you kind of have to look into the resources that are available. So, for example, like right now, we actually have a new behavioral health coach that we partnered to get from Cigna, who is our current medical carrier. And so this behavioral health coach is at No charge to our employees is actually covered by Cigna and they partner with the company called EverNorth to provide it. And so they can come and see them for, or see her, for not just ⁓ general questions about their health, but they can actually get assistance with any chronic conditions that they're experiencing, any treatment plans that they're on, if they would like to.

engage in weight loss strategy, she can help out with that, help them with the plan, actually, you know, weigh them in everything and get them going. And then on top of that provides some behavioral health coaching as well to our staff and do like group sessions, individual sessions, and that's totally free to our employees. So those are some ways that we are trying to be creative when it comes to not just benefits, but the compensation piece as well, because that, you know, again, that's more money that they or less money that they would have to spend on actually seeing, you know, health care professional unless it is something that they truly need more of a diagnosis on, a little bit more in-depth treatment and ⁓ assistance with.

But just that general being able to get them started and help them out with what they're currently doing, then we have someone, again, free for them that can provide that. And then, again, less that they're paying out of pocket. Kelsey Willock It brings up such a good topic, is under ⁓ squeezes in terms of budget. It can be really powerful to connect with your payer providers in seeing how they can help deliver additional value.

We see a lot of this, whether it's well-being stipends and beyond, preferred partners that they've worked with. imagine Evernorth was likely one of them, or perhaps you brought them in to tap into that SGMA budget. So it's a really great strategy to deliver that value even when Jessica O'Leary Mm-hmm. Yeah.

Kelsey Willock facing those budget concerns. Jessica O'Leary Oh yeah, for sure. I mean, a lot of school districts right now, they are facing, you know, budget restrictions, but still trying to maintain the proper amount of teachers in order to support students and regular administrative staff to support, you know, all the educators and instructional staff that we need in order to make the whole district function. So it's just those things you kind of have to consider, you know, as to what other resources are out there.

How can we be more creative? when it comes to maximizing benefits. Kelsey Willock When you think about compensation and benefits today, where do you see the breakdown most often happen? Jessica O'Leary ⁓ I think it's that a lot of employers sometimes don't see it as being like that total package.

They just worry about the cash benefit because of course that's what people want. That's what they work for because they have living expenses they need to take for the cash option. know, cash compensation is the means to an end. But you also have to look at what's the return on investment for the employee.

And so that's what kind of brings the whole total compensation package together. and bridges that gap. So it's like, okay, if I'm spending for some people, could just be eight, but some people are spending 10 hours a day and that's not even including commuting to and from work. So when it comes to me giving you all these hours of my life in order to help your organization or your corporation be profitable and successful, what do I get for that?

And so we kind of have to think into more as to beyond just the cash compensation, what else can we provide? So maybe beyond benefits, know, maximizing benefits, but it's like, Can we provide tuition reimbursements for those early career professionals? Or what training can we provide? How can we incentivize training?

It's like I was saying, know, gas cards, grocery gift cards, you know, like things like that that will actually help them out in the long run. And that's less money that they're spending from their actual pay just to get by, you know, and handle their day-to-day expenses. So I think just kind of considering that more than just the cash, it's kind of, again, the return on investment. What else can we provide that benefits them and will keep them coming back because they see that there's other ways that we're investing in them beyond just the paycheck.

Kelsey Willock Have you found ways that have allowed you to successfully, know, really help them better understand the total rewards package? I'm seeing a lot of, you know, build by tools. I'm curious what you're specifically seeing work. Jessica O'Leary Yes.

⁓ I think that's something that still is a challenge for us. think the allocation, the education piece is huge right now. I know for us that I'm trying to work on creating like an actual total rewards breakdown that shows employees beyond like what we pay you in your salary. What else is considered part of your, I'm sorry, total reward statement that actually shows beyond salary.

what exactly goes into their compensation. So what we contribute for benefits, what we contribute towards any other stipends or grants that we may provide to further their education, things like that, just to help them out so that they can better see exactly where all that money that we put aside for compensation, what else is it going to, to again, shows like what we're investing in them and their employment here. Kelsey Willock That makes a lot of sense. It can be as ⁓ simple as put it all in one place.

Total reward statements can be so effective if they can really break down what's the value that I'm actually receiving from the benefits to rewards beyond cash itself. Jessica O'Leary No. yeah, transparency is key right now and a lot of employees like they want that they want to see that and see exactly where is that money that you're saying you're paying me. Where exactly is it going?

So yeah, they want to see that. Kelsey Willock Benefits themselves have gone through a lot of really interesting changes. We're seeing a lot of really cool, new, interesting vendors emerge in the market. What's change that you've seen in benefits, either at this company or prior employers that you've worked at, that you've seen go from really just attracting talent to transforming the lives of employees?

Jessica O'Leary Yes. What I'm noticing now is that employee assistance programs are actually expanding ⁓ their offerings. So, you know, no longer the limitation of just three sessions for mental health counseling. Now they're actually, some are offering unlimited counseling, or they're more willing to negotiate with potential clients on how they can maximize that for ⁓ their employees.

Additionally, I'm seeing things like advance pay programs. So like with your payroll or HRIS system they may actually allow you to advance your paycheck so you can get paid sooner. Now, of course, that will impact your pay on payday because they have to kind of make up the difference, but allowing you to have access to your payment earlier for employees that have a gap in or live in paycheck to paycheck to just help them out in that way. That's something I'll send them seeing.

And then also at my last employer at City of Carrollton, something I love was the employee clinic and family members that were enrolled in medical plan could go and be seen there as well. So I think a clinic offering that at least addresses acute care and preventive care is awesome. Then it's at no cost to employees. can even try to fill prescriptions there.

So things like that, that kind of help them manage the day-to-day aspects of their life. And then of course, help address when they unfortunately kind of need access to money sooner and they don't want to go in debt in order to access it. So things like that that are kind of meeting those needs and gaps is what I'm seeing a lot. Kelsey Willock You know, it's such an important concept given financial stress is so high right now.

You you mentioned the importance of really health and well-being, mental health, and that financial health is so much so a part of that. It's not just the physical, it's not just the mental, it's also, you know, can I put food on the table? Conversation is going on right now. Jessica O'Leary Mm-hmm.

Kelsey Willock When introducing new programs or benefits, what's the kind of measurable impact you're seeking to have at the company? Jessica O'Leary Definitely hoping that it adds to retention. So I'm looking at that, you know, we have our exit surveys and then there, you know, we ask, you know, what were your, what was your reason for leaving the organization? So, you know, I hope that we're able to keep them because the last thing that they want to lose is their benefits because of all the things that we're offering them that competitively, you know, other ⁓ organizations may not offer.

So that will keep them. And again, it reduces the amount of out-of-pocket costs. So again, it maximizes what they have at the end of paying all their bills and everything, that it's not all going to medical costs or on top of the regular living expenses that they have. So that's something that I'm hoping.

And again, I think just the level of satisfaction of one less thing that they have to worry about. is when it comes to anything related to their benefits and even their compensation, because at least for what we're providing, it's adequate. And then they see that we truly are investing in them as an employee. Kelsey Willock It makes me think of the clinic concept that you had brought up, making people's lives easier, whether it's reducing the friction of time to get to care can be so phenomenally impactful.

And people remember those things. does. And I remember at previous employers, these seemingly small things that become a part of the big picture of why you chose that company in the first place and decided to stay there. So this is a hard question not to ask.

So I'm curious your thoughts on it. What compensation and benefits trends do you think are going to shape the employee experience most over the next year? Jessica O'Leary think honestly just the level of negotiating power that employees will be able to have more so when it comes to benefits and compensation. Again, them understanding like, if I'm putting in all these hours to you, what do I get out of it?

And so employers now, like I said, beyond just my paycheck, like what else do I get for working here? I think, again, employers are gonna need to be more creative because employees are seeing. or paying more attention to that, especially with all the layoffs going on. They're like, I've given years to this company and I've gotten nothing.

So beyond that, what else can you do for me? I think that's something that's gonna start trending more is I'm looking again into their own return on investment into you as an employer, how you're investing into me as an employee. Another thing is just being more or wanting employers to be more creative in what they're offering when it comes to benefits and being more resourceful to provide more resources that are free to the employees. I know we still talk about AI and all its advances.

I think it'll be more into a tool that helps employees better find options that are more suitable to their current needs. So I think that's another thing that will be trending as well with our broker. We've talked about improving our website, but then also there's a new benefits enrollment tool that uses AI to help employees actually select their benefits based off the plans that we have. So they can start answering questions from the tool, ask them kind of about their current health ⁓ condition, their needs, families, conditions, and then saying, okay, based off of this and what you need, looks like you should enroll in health plan A.

⁓ So just helping them there to kind of take that load off of the decision making. It's like, this is what I got going on. Please make the choice for me and tell me how much it is. So I think that will be something that trends and continues to trend going forward.

Kelsey Willock Yeah, you know that the personalization of benefits I like myself I get personally excited. I think we can all think about the times in which open enrollment comes around the corner and you have decision fatigue and not really sure how to make good decisions for yourself and maybe you're signing up on the final day to do so as so many of us do. I think that there's so much great, you know, support that AI can provide us recognizing these are the behaviors that we have.

Jessica O'Leary yeah. Yeah. Kelsey Willock Maybe we just need a little bit of push rather than assuming we know all the right answers for ourselves. Jessica O'Leary yeah, for sure.

Kelsey Willock So last question for you. What is a 30 day experiment our listeners could try to either boost financial wellness, well-being, or engagement of their companies? Jessica O'Leary Mm-hmm. I would say what we notice that gives the most engagement is just incentivizing things.

So it's like you can do this course or webinar and if you participate then maybe we can do like a raffle for a gift card again something that's more tangible that'll help them out. I think I've considered doing challenges, maybe a no-spend challenge, things like that. But I think right now, it's the biggest thing is just that general education and helping them understand how it all works. ⁓ For example, just one challenge we have right now is ⁓ employees going out on maternity leave.

But then ⁓ when they go out, they don't properly plan ahead. And so their leave will exceed the amount of PTO that they have. And so next thing you know, they're on leave without pay, like those things that help them understand financially how that can impact them. And I know this is great that you're having a baby, but still you kind of have to do the whole planning as to, you know, if I go on leave without pay, like, will I be able to pay my benefits premiums?

Will I be able to pay these out of pocket costs? Will I be able to pay for formula things, unexpected costs or supplies I didn't know I was going to need for my new little one? You know, those things you kind of have to think about. So we currently have like a virtual baby shower.

for those that are looking into starting a family or getting ready to go out on leave. That gives them an overview of everything, how maternity leave works, paid leave, all of that works. ⁓ So we wanna be more proactive in helping them understand beyond just this part of what policy is and you requesting FMLA all of that. When it comes to the financial portion of it, this is what you need to consider before you go out on leave or even before you decide to conceive.

this is what you might want to think about when it comes to your employment. And then just when it comes to your own personal life, things to consider financially that you may not have thought about as new parents. So ⁓ those are some challenges that we're kind of looking into that we currently have, and then some things that we are currently looking into. But again, the biggest challenge I would say is just work on trying to incentivize it more.

Again, people want something, so kind of getting them something that'll help them out, even if it's temporarily. that will definitely get them engaged. Our employees love to give cards and raffles that we have at our benefits fair. It gets them to come over to the table and talk to our carriers about their plans.

Again, what other resources and things are offered to them for being a part of the medical plan or dental, what have you. So if you give them a nice shiny Amazon card. that helps. And I think it retains more and then they, you know, want to come back because they know, usually there's something that they're offering.

So let me come and see what else I can learn and get from them. Kelsey Willock And a fun fact is an Amazon $20 gift card is actually worth mentally more than $20 in flash, which is a very interesting concept that, you know, deserves its own ⁓ behavioral psychology analysis, but people love gift cards. Jessica O'Leary Great. Mm-hmm.

Nice dopamine boost. Kelsey Willock It is a nice dopamine boost and super tangible to take away for our listeners. So thank you so much, Jessica, for the conversation. I learned so much from you.

Where can our listeners connect with you beyond this conversation? Jessica O'Leary yeah. They can find me on LinkedIn, Jessica O’Leary. I think I have MBA after my name.

I'm more than willing and happy to connect with anybody who'd like to kind of share some ideas and plan and all of that. Kelsey Willock We'll definitely go connect with Jessica if you've been listening. Thank you so much again. I hope you have a wonderful rest of your afternoon.

Jessica O'Leary You too, thanks for having me.